‘Poking Holes’ Singer Emily Warren Talks About Heartbreaking Songs, Dating and More

Also, the singer-songwriter is totally crushing on Don Draper.

Emily Warren doesn’t just sing songs about hypothetical love and messy situations – she’s lived them. Yes, she even reveals the no-so-pretty, quite ugly, uncomfortable stuff. The recording artist just released her latest single, Poking Holes, on October 13.

“My song Poking Holes is about how little things that you brush under the rug in a relationship have the capacity to do real damage to the big picture,” says Warren.

Although she’s just 25 years old, the New York City native has a deep understanding for society’s current romantic climate.

“I think there's actually quite a lot of pressure on people to be in relationships, and I was single for pretty much my whole life, until recently, so I know what that feels like,” she reveals. “And I just want to say that being single is not a negative thing, nor should it define you or how you view yourself in any way. As a matter of fact, it can be f----ing sick to have the time to figure out who you are without having to learn that in the context of anyone else — so enjoy it!” 

Amen, sister.

Read on for our one-on-one chat with the songstress, to learn about the hardest thing she’s written, an embarrassing moment from her past, and the most romantic thing someone has done for her.

What’s your favorite love, or heartbreak, song that you’ve written?

I've got some super emo heartbreak jams — and positive love songs, for that matter — that will be coming out on my album. But, probably my favorite that's out is a song I wrote with Astrid S. called I Don't Wanna Know, which is on her EP. I love this song, because the actual process of writing it was a big release for all involved, and it was a super emotional and rewarding session where I feel like we both really got something off of our chests. For me, I was in the middle of being intensely heartbroken and what was most painful was imagining the person I'd been with being happy and fine and moving on while I was still hurting. I've since calmed down, and he's back in my life, but these things take time! 

What has been the hardest thing to write and sing about?

I think the hardest thing to do is be vulnerable and honest, but I also think the things that are the hardest to say are exactly what you should be saying. It takes quite a bit of courage, and confidence, but if you say something truly personal, you have a great chance of connecting with other people who have felt the exact same things, and providing yourself and others with the comfort in knowing we're not alone. Music has done that for me countless times, so I'm always trying to pay that forward. 

Tell us about a time you wrote a song, or a lyric, about someone and performed it for them or had them listen to it.

Oh, man. This is something I do legitimately all the time. I remember in fifth grade, my friend showed my crush the lyrics to a song I had written about him. It was humiliating! But in my relationship now, my boyfriend actually produces a lot of my songs, and he fully knows they're about him and it's a beautiful thing. He's really very open and supportive, so it doesn't cause problems between us — it only creates more honesty and communication. But, I think that takes a very special kind of person. 

Are there any songs you’ve recorded that you don’t perform live?

Definitely — hundreds. But not all of them are great. I like to think of writing songs as working a muscle. I figure: if I write 50 songs, it's easy to step back and pick out the best 10, versus going with the first ones I write — but that's just my way of doing it. And I love writing, so it's really not a chore for me. 

What’s the most difficult thing about maintaining relationships while on the road?

I think probably the time difference and scheduling make it most difficult. If the window of time you can talk doesn't perfectly line up with theirs, it's easy to lose touch for a few days and feel distant. But at the same time, my boyfriend and I are genuinely psyched for each other's successes so not always being able to communicate is sort of the trade-off for being with someone who is killing it. 

Do you prefer to date musicians, artists, or creative people, or not so much?

I don't know if I set out to have it one way or the other, I'm sure there are benefits to both, but in my experience, I think it makes it easier when I don't have to explain myself because my boyfriend understands how consuming this career can be because he's in the same boat. I do think that something we are really good about is bonding over lots of things outside of music, so there is a separation and it's not always one thing. 

What’s the most romantic thing someone has done for you?

Write a song about me! 

What’s the most romantic thing you’ve done for someone else?

Write a song about them! 

Who is your celebrity crush? 

Don Draper in Mad Men almost purely because of his outfits. And no, I haven't met him but if he existed, I think I'd like to. 

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